Biodegradable unsaturated polyesters containing2,3-butanediol for engineering applications: Synthesis, characterization and performances

Hu, Xiaoran; Shen, Xiaolin; Huang, Mengfei; Liu, Chaohao; Geng, Yiting; Wang, Runguo; Xu, Riwei; He, Qinggang; Zhang, Liqun

doi:10.1016/j.polymer.2016.01.007

Cited by 27 publications

(23 citation statements)

References 29 publications

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“…31 recently studied the esterification kinetics between 2,3-butanediol and 1,4-butanediol with adipic acid and described the synthesis of (co)polyesters from this mixture of diols. 32 In this study, the polyesters were prepared in bulk by copolymerization of DVG (mixture of (±) and meso) with dimethylsuccinate (DMSu) or dimethylsebacate (DMSe), as bio-sourced diesters (Scheme 2). Several catalysts were tested such as 1,5,7-triazabicyclo [4.4.0]dec-5-ene (TBD), sodium methanolate (MeONa), titanium butoxide (Ti(OBu)4) and titanium isopropoxide (Ti(O i Pr)4), which are commonly used in polyester synthesis.…”

Section: Dvg Polymerization Via Hydroxyl Reactivity: Example Of Pomentioning

confidence: 99%

Divinylglycol, a Glycerol-Based Monomer: Valorization, Properties, and Applications

Bonnot

Len

Grau

et al. 2018

ACS Symposium Series

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In the context of the development of bio-refineries, glycerol and its derivatives are coproducts of the oleochemistry for which new valorization routes must be found. In this study, the polymerizability of divinylglycol (DVG), a symmetrical C-6 glycerol derivative which bears a vicinal diol and two vinyl functions was studied. The reactivity of the hydroxyl and vinyl functions of DVG through polycondensation and polyaddition reactions was investigated. In a first step, the synthesis of polyesters was carried out by reaction of DVG with various biosourced diesters. In a second route, DVG was polymerized through its vinyl functions by ADMET and thiol-ene addition. Finally, three-dimensional epoxy-amine networks were prepared from a series of diamines and bis-epoxidized DVG, the latter being prepared by oxidation of the DVG double bonds. These different polymerization reactions showed that DVG double bonds were more reactive than the alcohol ones and that a panel of original polymers could be obtained from this bio-sourced synthon. IntroductionPolymers are ubiquitous in our daily lives; the automotive, packaging, health and textile sectors, to name just a few of them, are meaningful. With the depletion of fossil resources and environmental concerns, the search for more sustainable solutions is becoming a necessity. Since the beginning of the 21st century, bio-sourced chemistry has been widely expending with the valorization of biomass, which is an abundant source of carbon structures. 1 In this regard, the concept of a biorefinery was created with the objective of producing feed, food, fuels and molecule platforms for industry. 2 Vegetable oils are the second renewable resource used after ligno-cellulosic biomass. 3 Vegetable oils are inexpensive, non-toxic and have a large potential as precursors of bio-based polymers. These oils are composed of triglycerides, which after reaction with an alcohol, water or a base will produce three molecules of fatty acids (or fatty esters) and a molecule of glycerol. Fatty acids are widely studied as precursors of thermoplastic or thermosetting polymers. 4,5 Glycerol is a simple, non-toxic and versatile molecule that provides access to a wide range of high-value bio-based molecules. 6 Recently, Len and coll. developed an eco-responsible synthesis of divinylglycol (DVG). 7 Divinylglycol (DVG) also called 1,5-hexadiene-3,4-diol is a symmetrical C-6 monomer which bears a vicinal diol and two vinyl functions. It can be synthesized from mannitol 8-10 or tartaric acid, 11 but this requires protection/deprotection steps and a rather low yield is obtained (20 to 52%). A third route to synthesize DVG is possible by a pinacol coupling of acrolein with a yield of 90% (Scheme 1). 12,13 Acrolein can be synthesized from glycerol but this molecule is toxic; Len and coll. then proposed a direct synthesis of DVG from glycerol. 7

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Section: Dvg Polymerization Via Hydroxyl Reactivity: Example Of Pomentioning

confidence: 99%

Divinylglycol, a Glycerol-Based Monomer: Valorization, Properties, and Applications

Bonnot

Len

Grau

et al. 2018

ACS Symposium Series

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“…Spider dragline silk has been fascinating human-being for thousands of years due to its excellent mechanical properties [1][2][3][4][5][6][7][8][9][10][11][12], and it is a source for biomaterials [13][14][15][16] for tissue engineering applications [17][18][19], and many methods have been proposed to produce artificial fibers mimicking the natural silks [20,21]. The classical approach is to use spider silk proteins to fabricate nanofibers by the electrospinning, though some properties can be enhanced, but it is far behind the natural silks.…”

Section: Introductionmentioning

confidence: 99%

Wetting and supercontraction properties of spider-based nanofibers

Tian

Zhou

et al. 2019

THERM SCI

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“…For example, suberin is a natural polymer that is used to produce novel linear and crosslinked bio‐polyesters through a transesterification process . Bio‐based polymers have also been synthesized from vegetable oils, including castor oil, and soybean oil, for the production of polyesters. Recently, lignocellulosic biomass (lignin polyol) was functionalized with propylene carbonate (PC) for use as replacement to conventional monomers for the synthesis of polyurethanes and polyesters…”

Section: Introductionmentioning

confidence: 99%

Sustainable poly(ether amide)s from lignin‐derived precursors

Saenz

Scott

2018

J. Polym. Sci. Part A: Polym. Chem.

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In recent years, there have been concerted efforts to replace petrochemical products with those from renewable sources due to the unsustainability of petroleum feedstock, and the continued volatility in the price. This work describes the synthesis and thermal properties of two new lignin‐derived poly(ether‐amide)s as alternative thermoplastics to petroleum‐based commodities. Poly‐4‐(2‐aminoethoxy)benzoate (PEAB) and poly‐4‐(2‐aminoethoxy)‐3‐methoxybenzoate (PEAV) are synthesized by a melt polycondensation and characterized by 1H NMR spectroscopy and thermal analysis. The number average molecular weight (Mn) of the polymers are estimated from the 1H NMR spectroscopy analysis, and were shown to be 4100 and 12,000 g/mol for PEAB and PEAV respectively. The PEAB had a higher decomposition temperature (Td) as well as glass transition temperature (Tg) compared to PEAV; albeit, with a lower molecular weight. The polymers’ Td were in the range of 330 °C–380 °C and the Tg were between 100 °C and 120 °C. The thermal properties of the polymers are in the desirable range for thermoplastic materials used in the packaging, storage, and coating industries. Furthermore, the polymers are susceptible to degradation under acidic conditions in a short period; a property that is highly desirable for degradable polymers. © 2018 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2018, 56, 2154–2160

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Biodegradable unsaturated polyesters containing2,3-butanediol for engineering applications: Synthesis, characterization and performances

Cited by 27 publications

References 29 publications

Divinylglycol, a Glycerol-Based Monomer: Valorization, Properties, and Applications

Divinylglycol, a Glycerol-Based Monomer: Valorization, Properties, and Applications

Wetting and supercontraction properties of spider-based nanofibers

Sustainable poly(ether amide)s from lignin‐derived precursors

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